2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime

Base Information

• Chemical Name: 2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime
• CAS No.: 1426924-87-9
• Molecular Formula: C₂₂H₂₆ClNO₇
• Molecular Weight: 451.904
• Mol file: 1426924-87-9.mol

Synonyms:2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime

Chemical Property of 2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime

There total 11 articles about 2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.2%

(2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (1426924-91-5) → 2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime (1426924-87-9)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 1h;

Reference yield:

(3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1416165-10-0) → 2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime (1426924-87-9)

Guidance literature:

Multi-step reaction with 6 steps

1: zinc(II) oxide / 1 h / 60 °C

2: caesium carbonate / N,N-dimethyl-formamide / 36 h / 20 °C

3: acetic acid / tetrahydrofuran; water / 24 h / 0 - 20 °C

4: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.08 h / -78 °C / Inert atmosphere

5: pyridine; sodium acetate / ethanol / 5 h / Inert atmosphere; Reflux

6: lithium hydroxide monohydrate / water; methanol / 1 h / 0 - 20 °C

With pyridine; oxalyl dichloride; lithium hydroxide monohydrate; sodium acetate; caesium carbonate; acetic acid; zinc(II) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

[4-(5-bromo-2-chloro-benzyl)-phenoxy]-tert-butyl-dimethyl-silane (864070-19-9) → 2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime (1426924-87-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 18 h / -78 - 20 °C

2.1: water; acetic acid / 22 h / 110 °C

2.2: 16 h / 20 °C

3.1: acetic acid; hydrogen bromide / water; dichloromethane / 2.5 h / 20 °C

4.1: zinc(II) oxide / 1 h / 60 °C

5.1: caesium carbonate / N,N-dimethyl-formamide / 36 h / 20 °C

6.1: acetic acid / tetrahydrofuran; water / 24 h / 0 - 20 °C

7.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.08 h / -78 °C / Inert atmosphere

8.1: pyridine; sodium acetate / ethanol / 5 h / Inert atmosphere; Reflux

9.1: lithium hydroxide monohydrate / water; methanol / 1 h / 0 - 20 °C

With pyridine; n-butyllithium; oxalyl dichloride; lithium hydroxide monohydrate; hydrogen bromide; sodium acetate; caesium carbonate; acetic acid; zinc(II) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

[4-(5-bromo-2-chloro-benzyl)-phenoxy]-tert-butyl-dimethyl-silane

(3aS,5R,6R,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

(3S,4R,5S,6S)-6-(3-(4-acetoxybenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

(3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate